Global Patent Index - EP 4335513 A3

EP 4335513 A3 20240508 - CRYSTAL CHARACTERISTICS, PREPARATION PROCESSES AND ANTICANCER APPLICATIONS OF 17BETA-NERIIFOLIN CRYSTAL FORMS

Title (en)

CRYSTAL CHARACTERISTICS, PREPARATION PROCESSES AND ANTICANCER APPLICATIONS OF 17BETA-NERIIFOLIN CRYSTAL FORMS

Title (de)

KRISTALLEIGENSCHAFTEN, HERSTELLUNGSVERFAHREN UND ANTIKREBSANWENDUNGEN VON 17BETA-NERIIFOLIN-KRISTALLFORMEN

Title (fr)

CARACTÉRISTIQUES CRISTALLINES, PROCÉDÉS DE PRÉPARATION ET APPLICATIONS ANTICANCÉREUSES DE FORMES CRISTALLINES DE 17BÊTA-NERIIFOLINE

Publication

EP 4335513 A3 20240508 (EN)

Application

EP 24150900 A 20180516

Priority

  • CN 201710358086 A 20170519
  • EP 18802832 A 20180516
  • CN 2018087031 W 20180516

Abstract (en)

The present invention provides the preparation processes for several crystal forms of the compound 17beta-Neriifolin (17bNF) and use thereof in anti-tumor applications. The present invention provides preparation processes for four kinds of non-solvated crystal forms, amorphous powders and eleven kinds of solvated crystalline solids, including ethanol-solvated ones, of 17bNF that are not present in nature, and the identification and characterization of these crystal forms by crystallographic research methods such as X-ray powder diffraction. In addition, through vivo anti-tumor experiments with five of the crystal forms in nude mice, we provide anti-tumor and anti-cancer applications of the crystal forms of 17bNF.

IPC 8 full level

C07J 19/00 (2006.01); A61K 31/58 (2006.01); A61P 35/00 (2006.01)

CPC (source: CN EP US)

A61P 35/00 (2018.01 - EP); C07J 19/005 (2013.01 - CN EP US); C07B 2200/13 (2013.01 - CN EP US)

Citation (search report)

  • [I] HOONG-KUN FUN ET AL: "Absolute configuration of 14beta-hydroxy-3beta-O-(L-thevetosyl)-5beta-card-20(22)-enolide chloroform disolvate", ACTA CRYSTALLOGRAPHICA SECTION E, vol. E59, no. 11, 15 October 2003 (2003-10-15), pages o1694 - o1696, XP055767241, DOI: 10.1107/S1600536803021822
  • [I] SUCHADA CHANTRAPROMMA ET AL: "Bis[14b-hydroxy-3b-O-(L-thevetosyl)- 5b-card-20(22)-enolide] methanol solvate monohydrate and 3b-O-(L-20 - o-acetylthevetosyl)-14b-hydroxy-5bcard-20(22)-enolide", ACTA CRYSTALLOGRAPHICA SECTION C. CRYSTAL STRUCTURE COMMUNICATIONS, vol. C59, no. 2, 18 January 2003 (2003-01-18), DK, pages o68 - o70, XP055766514, ISSN: 0108-2701, DOI: 10.1107/S0108270102023065
  • [I] MCLAUGHLIN J L ET AL: "Neriifolin and 2' -Acetylneriifolin: Insecticidal and Cytotoxic Agents of Thevetia thevetioides Seeds", JNAL OF ECONOMIC ENTOMOLOGY,, vol. 73, no. 3, 1 June 1980 (1980-06-01), pages 398 - 402, XP001466454
  • [I] LANG HUIYIN ET AL: "STUDIES ON THE CARDIAC GLYCOSIDES OF THEVETIA PERUVIANA MERR.SYN.THEVETIA NERIIFOLIA JUSS.--II.ISOLATION AND IDENTIFICATION OF CERBERIN,RUVOSIDE,AND A NEW CARDIAC GLYCOSIDE--PERUSITIN", ACTA PHARMACEUTICA SINICA, YAOXUE XUEBAO, CN, vol. 11, no. 7, 31 December 1964 (1964-12-31), pages 464 - 472, XP009517901, ISSN: 0513-4870, DOI: 10.16438/J.0513-4870.1964.07.006
  • [I] H HELFENBERGER ET AL: "197. Thevetin. I. Glykoside und Aglykone", HELVETICA CHIMICA ACTA, vol. 31, no. 6, 1 January 1948 (1948-01-01), pages 1470 - 1482, XP055766524
  • [I] RANGASWAMI S ET AL: "Active principles of Cerbera odollam", JOURNAL OF SCIENTIFIC AND INDUSTRIAL RESEARCH, SCIENTIFIC PUBLISHERS, INDIA, vol. 16B, 1 January 1957 (1957-01-01), pages 209 - 212, XP009525018, ISSN: 0022-4456
  • [XI] XIAO-PO Z ET AL: "Chemical constituents from the leaves of Cerbera manghas", ASIAN PACIFIC JOURNAL OF TROPICAL MEDICINE, HAINAN MEDICAL COLLEGE, SINGAPORE, vol. 3, no. 2, 1 February 2010 (2010-02-01), pages 109 - 111, XP027245620, ISSN: 1995-7645, [retrieved on 20100201]
  • [I] LEI LEI CAO ET AL: "Chemical constituents in fruits of mangrove plant Cerbera manghas L.", ZHONGGUO YAOXUE ZAZHI, vol. 48, no. 13, 1 January 2013 (2013-01-01), pages 1052 - 1056, XP055767269
  • [I] R BLOCH ET AL: "88. Die Konstitution von Cerberosid (Thevetin B), Thevetin A und Peruvosid", HELVETICA CHIMICA ACTA, vol. 43, no. 3, 1 January 1960 (1960-01-01), pages 652 - 658, XP055767193
  • [I] MARCEL FREREJACQUE: "La nériifoline, nouvel hétéroside digitalique de Thevetia neriifolia", COMPTES RENDUS HEBDOMADAIRES DES SÉANCES DE L'ACADÉMIE DES SCIENCES, vol. 221, 1 January 1945 (1945-01-01), pages 645 - 646, XP055767573
  • [I] EL TANBOULY N D ET AL: "Cytotoxic cardiac glycosides from Thevetia neriifolia Juss. roots", BULLETIN OF THE FACULTY OF PHARMACY, CAIRO UNIVERSITY, FACULTY OF PHARMACY, EGYPT, vol. 38, no. 3, 1 January 2000 (2000-01-01), pages 103 - 106, XP009525049, ISSN: 0575-1373

Designated contracting state (EPC)

AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

DOCDB simple family (publication)

WO 2018210252 A1 20181122; CA 3100875 A1 20181122; CN 108948119 A 20181207; CN 108948119 B 20231121; CN 117756875 A 20240326; EP 3625242 A1 20200325; EP 3625242 A4 20210707; EP 4335513 A2 20240313; EP 4335513 A3 20240508; US 11091510 B2 20210817; US 2020157139 A1 20200521

DOCDB simple family (application)

CN 2018087031 W 20180516; CA 3100875 A 20180516; CN 201710358086 A 20170519; CN 202311447249 A 20170519; EP 18802832 A 20180516; EP 24150900 A 20180516; US 201916688169 A 20191119